Due to the social, political, and religious upheavals occurring across Europe in the Early Modern period, many writers were exploring the proper relationship between citizens and political and religious leaders. While some writers encouraged citizens to give unconditional loyalty to local and national leaders, Shakespeare has a pattern of endorsing citizen rebellion as a moral means to overthrow tyrannical rulers. By exploring Richard III, Measure for Measure, and Julius Caesar, I argue that Shakespeare is developing a taxonomy of citizen responses to a tyrannical leader and teaches citizens that a moral rebellion can be launched against a tyrant when a citizen embraces personal responsibility, accepts the power of rhetoric over violence, and overcomes the filtering effects of nostalgia. To demonstrate that Shakespeare is deliberately entering the conversation about a citizen's reaction to a tyrant, I provide information about how a tyrant is defined in the Early Modern period. I synthesize the scholarship on relevant texts in the period and explain how all three leaders in the aforementioned plays support that definition of tyranny. Then I focus on each play's surrounding characters to discuss the motivations and reactions of rebellious and obedient citizens. Finally, I conclude each section with an analysis of the repercussions of the citizen's actions and evaluate the lessons that Shakespeare is consistently promoting about moral rebellion.